Curable composition

ABSTRACT

A composition including at least one polymer containing silane groups, at least one epoxy resin, and at least one amine of the formula (I). The composition is low in odor, low in toxicity, and highly workable. It enables low-emission products which cure rapidly at ambient temperature to form macroscopically homogeneous films or bodies having good mechanical properties, high thermal stability and good adhesion properties, the mechanical properties being able to be adjusted from very elastic through to tough elastic. The composition is especially suitable as adhesive and/or sealant or coating.

TECHNICAL FIELD

The invention relates to amine hardeners and curable compositions basedon a combination of polymer containing silane groups and of epoxy resin,and also to the use thereof as adhesive, sealant, coating, castingcompound or matrix resin.

PRIOR ART

As coatings and high-strength adhesives it is common to usetwo-component polyurethane systems. These systems cure rapidly atambient temperature and form a tough elastic material of high strength,but contain low molecular mass isocyanates that are harmful to health,and may form blisters when cured in a humid environment. In a similarway, two-component epoxy resin systems are also used. These systemsattain very high strengths, but are not tough elastic or elastic,instead having a high stiffness and relative brittleness and thereforenot being suitable for applications requiring a certain stretchability.Oftentimes, moreover, they contain amines that are harmful to health,and in a humid environment are sensitive to what are referred to asblushing effects, possibly resulting in detractions from surfacequality, adhesion and strength. Curable materials based onsilane-functional polymers are known from application as elasticsealants and adhesives. They are usually in one-component formulationsand they crosslink through reaction with atmospheric moisture. They arenotable for relatively low toxicity, blister-free curing and high forcesof adhesion, but are relatively slow to cure and attain only lowstrengths. Their resistance to tearing is low, and they are thereforedecidedly brittle. Moreover, their thermal stability is relatively low.They are therefore less suitable as coatings and high-strengthadhesives. Also known are two-component systems based on a combinationof silane-functional polymers with epoxy resins—from EP 0 186 191 and EP0 370 464, for example. Such systems achieve greater strength andtoughness, and also heat resistance, than those based onsilane-functional polymers alone, but are still capable of beingimproved. To cure the epoxy resin, the known systems contain lowmolecular mass amines or Mannich bases. This gives them increasedtoxicity and a pronounced and unpleasant amine odor. Furthermore, onapplication in the cold and/or under high atmospheric humidity, theyhave a tendency toward curing defects, which are caused by formation ofsalts (carbamatization) by the amines present with CO₂ (known asblushing) and are manifested in particular in the form of reducedultimate hardness. Moreover, they have a relatively high viscosity andare therefore not easy to work unless diluents are used, resulting inincreased emissions.

SUMMARY OF THE INVENTION

It is an object of the present invention to provide a curable materialwhich is low in odor, low in toxicity and has ready workability andwhich enables low-emission products which cure rapidly at ambienttemperature to form macroscopically homogeneous films or bodies havinghigh strength and stretchability.

This object, surprisingly, is achieved by a composition as described inclaim 1. The composition is notable for a low odor and a low toxicity.Its viscosity is low and it exhibits hardly any tendency towardcarbamatization or blushing effects. As a two-component composition, ithas a long shelf life and, after mixing, cures rapidly and withoutblistering to form an elastic polymer of high strength which has highstability under hot conditions and under UV radiation. This combinationof properties enables low-emission products which are easy to apply andwork, which cure rapidly in a humid or cold environment, and do so toform highly mechanically robust plastics with an attractive surface thatare thermally stable, the possibility existing of adjusting themechanical properties from very elastic, with not too high a modulus ofelasticity and with high strength, through to tough elastic, with a veryhigh modulus of elasticity and a very high strength. The composition isalso advantageous especially when for reasons of occupational and healthprotection the products to be used are to be free of isocyanate.

A surprising feature of the composition of the invention are the goodmechanical properties, especially the high strength and high elongation,the low viscosity, and the attractive, nontacky surface. As a result ofthe low viscosity, the composition can be made particularly workable.

The composition of the invention is particularly suitable as adhesive,sealant, coating, casting compound or matrix resin in the constructionand manufacturing industries.

Further aspects of the invention are the subject of further independentclaims. Particularly preferred embodiments of the invention are thesubject of the dependent claims.

WAYS OF EXECUTING THE INVENTION

The invention provides a composition comprising

-   -   at least one polymer containing silane groups,    -   at least one epoxy resin, and    -   at least one amine of the formula (I)

-   -   where    -   A is an alkylene radical having 2 to 15 carbon atoms which        optionally contains one or more nitrogen atoms,    -   R each independently is a hydrogen or methyl or phenyl radical,    -   Q is a five-, six- or seven-membered cycloalkyl or aryl radical        optionally having an oxygen, sulfur or nitrogen atom in the ring        and having 4 to 7 carbon atoms,    -   Y represents identical or different radicals selected from the        group consisting of alkyl, alkoxy and dialkylamino having 1 to        18 carbon atoms,    -   m is 1 or 2, and    -   n is 0 or 1 or 2 or 3.

In the present document, the term “alkoxysilane group” or “silane group”for short refers to a silyl group which is bonded to an organic radicaland has one to three, especially two or three, hydrolyzable alkoxyradicals on the silicon atom.

Correspondingly, the term “organosilane” or “silane” for short refers toan organic compound which contains at least one silane group.

“Aminosilane”, “mercaptosilane”, “hydroxysilane” and “isocyanatosilane”refer respectively to organosilanes having one or more amino, mercapto,hydroxyl or isocyanate groups on the organic radical in addition to thesilane group.

The term “polyether containing silane groups” also encompasses polymerswhich contain silane groups and which, in addition to polyether units,may also contain urethane groups, urea groups or thiourethane groups.Such polyethers containing silane groups may also be referred to as“polyurethanes containing silane groups”.

Substance names beginning with “poly”, such as polyol or polyisocyanate,refer to substances containing, in a formal sense, two or more of thefunctional groups that occur in their name per molecule.

A “primary amino group” refers to an amino group which is bonded to asingle organic radical and bears two hydrogen atoms; a “secondary aminogroup” refers to an amino group which is bonded to two organic radicalswhich may also together be part of a ring and bears one hydrogen atom;and a “tertiary amino group” refers to an amino group which is bonded tothree organic radicals, two or three of which may also be part of one ormore rings, and does not bear any hydrogen atom.

An amine or polyamine is said to be “aliphatic” when its amino groupsare bonded to an aliphatic or cycloaliphatic or arylaliphatic radical.

An “amine hydrogen” refers to the hydrogen atoms of primary andsecondary amino groups.

An “amine hydrogen equivalent weight” refers to the mass of an amine oran amine-containing composition that contains one molar equivalent ofamine hydrogen.

“Molecular weight” refers to the molar mass (in g/mol) of a molecule.“Average molecular weight” is understood to mean the number-averageM_(n) of an oligomeric or polymeric mixture of molecules, which istypically determined by means of gel permeation chromatography (GPC)against polystyrene as standard.

“Viscosity” refers to the dynamic viscosity or shear viscosity which isdefined by the ratio between the shear stress and the shear rate (speedgradient) and is determined as described in the working examples.

A substance or composition is referred to as “storage-stable” or“storable” when it can be stored at room temperature in a suitablecontainer over a prolonged period, typically over at least 3 months upto 6 months or more, without any change in its application or serviceproperties to an extent relevant for service thereof, as a result of thestorage.

The abbreviation “VOC” stands for “volatile organic compounds”, i.e.volatile organic substances having a vapor pressure of at least 0.01 kPaat 293.14 K.

“Solvent” is a liquid which dissolves the polymer containing silanegroups and/or the epoxy resin and which is a VOC and contains no groupsthat are reactive toward silane or epoxide groups.

A dotted line in the formulae in this document in each case representsthe bond between a substituent and the corresponding molecular radical.

“Room temperature” refers to a temperature of 23° C.

The composition comprises at least one polymer containing silane groups.This is preferably an organic polymer containing silane groups, moreparticularly a polyolefin, poly(meth)acrylate or polyether or a mixedform of these polymers, each of which bears one or preferably more thanone silane group. The silane groups may be pendant from the chain orterminal.

In particular, the polymer containing silane groups is a polyethercontaining silane groups. This polyether preferably has a majority ofoxyalkylene units, more particularly 1,2-oxypropylene units.

The polymer containing silane groups is preferably liquid at roomtemperature.

The polymer containing silane groups has an average of preferably 1.3 to4, especially 1.5 to 3, more preferably 1.7 to 2.8, silane groups permolecule. The silane groups are preferably terminal.

Preferred silane groups are trimethoxysilane groups,dimethoxymethylsilane groups or triethoxysilane groups.

The polymer containing silane groups preferably has a mean molecularweight, determined by means of GPC against a polystyrene standard, inthe range from 1000 to 30 000 g/mol, especially from 2000 to 20 000g/mol.

The polymer containing silane groups preferably comprises end groups ofthe formula (II),

wherep stands for a value of 0 or 1 or 2, preferably 0 or 1, moreparticularly 0,R⁴ is a linear or branched, monovalent hydrocarbyl radical having 1 to 5carbon atoms,R⁵ is a linear or branched, monovalent hydrocarbyl radical having 1 to 8carbon atoms, especially methyl or ethyl,R⁶ is a linear or branched, divalent hydrocarbyl radical which has 1 to12 carbon atoms and which optionally contains cyclic and/or aromaticmoieties and optionally one or more heteroatoms, especially one or morenitrogen atoms,X is a divalent radical selected from —O—, —S—, —N(R⁷)—, —N(R⁷)—CO—,—O—CO—N(R⁷)—, —N(R⁷)—CO—O—, —N(R⁷)—CO—N(R⁷)—,—N(R⁷)—CO—O—CH(CH₃)—CO—N(R⁷)—, —N(R⁷)—CO—O—CH(R⁸)—CH₂—CH₂—CO—N(R⁷)— and—N(R⁷)—CO—O—CH(CH₃)—CH₂—O—CO—N(R⁷)—,

-   -   where    -   R⁷ is a hydrogen atom or is a linear or branched hydrocarbyl        radical which has 1 to 20 carbon atoms and which optionally        contains cyclic moieties, and which optionally contains an        alkoxysilyl group or ether or carboxylic ester groups,    -   and R⁸ is an unbranched alkyl radical having 1 to 6 carbon        atoms, more particularly methyl.

Preferably R⁴ is methyl or is ethyl or is isopropyl.

More preferably, R⁴ is methyl. Polymers of this kind containing silanegroups are particularly reactive.

More preferably, moreover, R⁴ is ethyl. Polymers of this kind containingsilane groups are particularly stable on storage and toxicologicallyadvantageous.

Preferably, R⁵ is methyl.

Preferably, R⁶ is 1,3-propylene or 1,4-butylene, where butylene may besubstituted by one or two methyl groups.

More preferably, R⁶ is 1,3-propylene.

Processes for preparing polyethers containing silane groups are known tothe person skilled in the art.

In one process, polyethers containing silane groups are obtainable fromthe reaction of polyethers containing allyl groups with hydrosilanes(hydrosilylation), optionally with chain extension using, for example,diisocyanates.

In another process, polyethers containing silane groups are obtainablefrom the copolymerization of alkylene oxides and epoxysilanes,optionally with chain extension using, for example, diisocyanates.

In a further process, polyethers containing silane groups are obtainablefrom the reaction of polyether polyols with isocyanatosilanes,optionally with chain extension using diisocyanates.

In a further process, polyethers containing silane groups are obtainablefrom the reaction of polyethers containing isocyanate groups, especiallyNCO-terminated urethane polyethers from the reaction of polyetherpolyols with a superstoichiometric amount of polyisocyanates, withaminosilanes, hydroxysilanes or mercaptosilanes. Polyethers containingsilane groups from this process are particularly preferred. This processenables the use of a multitude of inexpensive starting materials of goodcommercial availability, by means of which it is possible to obtaindifferent polymer properties, for example high stretchability, highstrength, low glass transition temperature, or high resistance tohydrolysis.

Preferred polyethers containing silane groups are obtainable from thereaction of NCO-terminated urethane polyethers with aminosilanes orhydroxysilanes. NCO-terminated urethane polyethers suitable for thispurpose are obtainable from the reaction of polyether polyols,especially polyoxyalkylenediols or polyoxyalkylenetriols, preferablypolyoxypropylenediols or polyoxypropylenetriols, with asuperstoichiometric amount of polyisocyanates, especially diisocyanates.

Preferably, the reaction between the polyisocyanate and the polyetherpolyol is conducted with exclusion of moisture at a temperature of 50°C. to 160° C., optionally in the presence of suitable catalysts, withmetered addition of the polyisocyanate in such a way that the isocyanategroups thereof are present in a stoichiometric excess in relation to thehydroxyl groups of the polyol. More particularly, the excess ofpolyisocyanate is chosen such that a content of free isocyanate groupsin the range from 0.1% to 10% by weight, preferably 0.2% to 5% byweight, more preferably 0.3% to 3% by weight, based on the overallpolymer, remains in the resulting urethane polyether after the reactionof all hydroxyl groups.

Preferred diisocyanates are selected from the group consisting ofhexamethylene 1,6-diisocyanate (HDI),1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (=isophoronediisocyanate or IPDI), tolylene 2,4- and 2,6-diisocyanate and anydesired mixtures of these isomers (TDI) and diphenylmethane 4,4′-, 2,4′-and 2,2′-diisocyanate and any desired mixtures of these isomers (MDI).Particular preference is given to IPDI or TDI. Most preferred is IPDI.In this way, polyethers containing silane groups with particularly goodlightfastness are obtained.

Especially suitable as polyether polyols are polyoxyalkylenediols orpolyoxyalkylenetriols having a degree of unsaturation lower than 0.02meq/g, especially lower than 0.01 meq/g, and an average molecular weightin the range from 400 to 25 000 g/mol, especially 1000 to 20 000 g/mol.

As well as polyether polyols, it is also possible to use proportions ofother polyols, especially polyacrylate polyols or polyester polyols, andalso low molecular weight diols or triols.

Suitable aminosilanes for the reaction with an NCO-terminated urethanepolyether are primary or secondary aminosilanes. Preference is given to3-aminopropyltrimethoxysilane, 3-aminopropyldimethoxymethylsilane,4-aminobutyltrimethoxysilane, 4-amino-3-methylbutyltrimethoxysilane,4-amino-3,3-dimethylbutyltrimethoxysilane,N-butyl-3-aminopropyltrimethoxysilane,N-phenyl-3-aminopropyltrimethoxysilane, adducts formed from primaryamino-silanes such as 3-aminopropyltrimethoxysilane,3-aminopropyldimethoxy-methylsilane orN-(2-aminoethyl)-3-aminopropyltrimethoxysilane and Michael acceptorssuch as acrylonitrile, (meth)acrylic esters, (meth)acrylamides, maleicor fumaric diesters, citraconic diesters or itaconic diesters,especially dimethyl or diethylN-(3-trimethoxysilylpropyl)aminosuccinate. Likewise suitable are analogsof the aminosilanes mentioned with ethoxy or isopropoxy groups in placeof the methoxy groups on the silicon.

Suitable hydroxysilanes for the reaction with an NCO-terminated urethanepolyether are especially obtainable from the addition of aminosilanesonto lactones or onto cyclic carbonates or onto lactides.

Preferred hydroxysilanes of this kind areN-(3-triethoxysilylpropyl)-2-hydroxypropanamide,N-(3-trimethoxysilylpropyl)-2-hydroxypropanamide,N-(3-triethoxysilylpropyl)-4-hydroxypentanamide,N-(3-triethoxysilylpropyl)-4-hydroxyoctanamide,N-(3-triethoxysilylpropyl)-5-hydroxydecanamide orN-(3-triethoxysilylpropyl)-2-hydroxypropyl carbamate.

Further suitable hydroxysilanes are obtainable from the addition ofaminosilanes onto epoxides or from the addition of amines ontoepoxysilanes. Preferred hydroxysilanes of this kind are2-morpholino-4(5)-(2-trimethoxysilylethyl)cyclohexan-1-ol,2-morpholino-4(5)-(2-triethoxysilyl-ethyl)cyclohexan-1-ol or1-morpholino-3-(3-(triethoxysilyl)propoxy)propan-2-ol.

Further suitable polyethers containing silane groups are commerciallyavailable products, especially the following: MS Polymer™ (from KanekaCorp.; especially the 5203H, 5303H, S227, S810, MA903 and S943products); MS Polymer™ or Silyl™ (from Kaneka Corp.; especially theSAT010, SAT030, SAT200, SAX350, SAX400, SAX725, MAX450, MAX951products); Excestar® (from Asahi Glass Co. Ltd.; especially the S2410,S2420, S3430, S3630 products); SPUR+* (from Momentive PerformanceMaterials; especially the 1010LM, 1015LM, 1050MM products); Vorasil™(from Dow Chemical Co.; especially the 602 and 604 products); Desmoseal®(from Covestro; especially the S XP 2458, S XP 2636, S XP 2749, S XP2774 and S XP 2821 products), TEGOPAC® (from Evonik Industries AG;especially the Seal 100, Bond 150, Bond 250 products), Polyvest® (fromEvonik; especially the EP ST-M and EP ST-E products), Polymer ST (fromHanse Chemie AG/Evonik Industries AG, especially the 47, 48, 61, 61LV,77, 80, 81 products); Geniosil® STP (from Wacker Chemie AG; especiallythe E10, E15, E30, E35 products) or Arufon (from Toagosei, especiallythe US-6100 or US-6170 products).

The amount of polymer containing silane groups in the composition ispreferably in the range from 5 to 80% by weight, more preferably in therange from 10 to 75% by weight, more particularly in the range from 15to 70% by weight.

The composition further comprises at least one epoxy resin.

Suitable epoxy resins are standard industrial epoxy resins. These areobtained in a known manner, for example from the oxidation of thecorresponding olefins or from the reaction of epichlorohydrin with thecorresponding polyols, polyphenols or amines.

Particularly suitable epoxy resins are what are called liquidpolyepoxide resins, referred to as “liquid resin” hereinafter. Thesehave a glass transition temperature below 25° C.

Likewise possible as epoxy resins are what are called solid resins whichhave a glass transition temperature above 25° C. and can be comminutedto powders that are pourable at 25° C.

Suitable epoxy resins are especially aromatic epoxy resins, especiallythe glycidylization products of:

-   -   bisphenol A, bisphenol F or bisphenol A/F, where A stands for        acetone and F for formaldehyde, which served as reactants for        preparation of these bisphenols. In the case of bisphenol F,        positional isomers may also be present, especially derived from        2,4′- or 2,2′-hydroxyphenylmethane.    -   dihydroxybenzene derivatives such as resorcinol, hydroquinone or        catechol;    -   further bisphenols or polyphenols such as        bis(4-hydroxy-3-methylphenyl)methane,        2,2-bis(4-hydroxy-3-methylphenyl)propane (bisphenol C),        bis(3,5-dimethyl-4-hydroxyphenyl)methane,        2,2-bis(3,5-dimethyl-4-hydroxyphenyl)propane,        2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane,        2,2-bis(4-hydroxy-3-tert-butylphenyl)propane,        2,2-bis(4-hydroxyphenyl)butane (bisphenol B),        3,3-bis(4-hydroxyphenyl)pentane, 3,4-bis(4-hydroxyphenyl)hexane,        4,4-bis(4-hydroxyphenyl)heptane,        2,4-bis(4-hydroxyphenyl)-2-methylbutane,        2,4-bis(3,5-dimethyl-4-hydroxyphenyl)-2-methylbutane,        1,1-bis(4-hydroxyphenyl)cyclohexane (bisphenol Z),        1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (bisphenol        TMC), 1,1-bis(4-hydroxyphenyl)-1-phenylethane,        1,4-bis[2-(4-hydroxyphenyl)-2-propyl]benzene (bisphenol P),        1,3-bis[2-(4-hydroxyphenyl)-2-propyl]benzene (bisphenol M),        4,4′-dihydroxydiphenyl (DOD), 4,4′-dihydroxybenzophenone,        bis(2-hydroxynaphth-1-yl)methane,        bis(4-hydroxynaphth-1-yl)methane, 1,5-dihydroxynaphthalene,        tris(4-hydroxyphenyl)methane,        1,1,2,2-tetrakis(4-hydroxyphenyl)ethane, bis(4-hydroxyphenyl)        ether or bis(4-hydroxyphenyl) sulfone;    -   condensation products of phenols with formaldehyde that are        obtained under acidic conditions, such as phenol novolaks or        cresol novolaks, also called bisphenol F novolaks;    -   aromatic amines such as aniline, toluidine, 4-aminophenol,        4,4′-methylenediphenyldiamine,        4,4′-methylenediphenyldi(N-methyl)amine,        4,4′-[1,4-phenylenebis(1-methylethylidene)]bisaniline        (bisaniline P) or        4,4′-[1,3-phenylenebis(1-methylethylidene)]bisaniline        (bisaniline M).

Further suitable epoxy resins are aliphatic or cycloaliphaticpolyepoxides, especially

-   -   glycidyl ethers of saturated or unsaturated, branched or        unbranched, cyclic or open-chain di-, tri- or tetrafunctional C₂        to C₃₀ alcohols, especially ethylene glycol, propylene glycol,        butylene glycol, hexanediol, octanediol, polypropylene glycols,        dimethylolcyclohexane, neopentyl glycol, dibromoneopentyl        glycol, castor oil, trimethylolpropane, trimethylolethane,        pentaerythritol, sorbitol or glycerol, or alkoxylated glycerol        or alkoxylated trimethylolpropane;    -   a hydrogenated bisphenol A, F or A/F liquid resin, or the        glycidylization products of hydrogenated bisphenol A, F or A/F;    -   an N-glycidyl derivative of amides or heterocyclic nitrogen        bases, such as triglycidyl cyanurate or triglycidyl        isocyanurate, or reaction products of epichlorohydrin with        hydantoin.    -   epoxy resins from the oxidation of olefins such as, in        particular, vinylcylohexene, dicyclopentadiene, cyclohexadiene,        cyclododecadiene, cyclododecatriene, isoprene, 1,5-hexadiene,        butadiene, polybutadiene or divinylbenzene.

A preferred epoxy resin is a liquid resin.

Particularly preferred as epoxy resin is a liquid resin based on abisphenol. Most preferred as epoxy resin is a liquid resin based on adiglycidyl ether of bisphenol A, of bisphenol F or of bisphenol A/F, ofthe kind commercially available, for example, from Dow, Huntsman orMomentive. These epoxy resins have readily manageable viscosity andenable high strengths and resistances. Such liquid resins may alsoinclude fractions of solid bisphenol A resin or phenol novolaks.

The composition preferably has an epoxy resin content in the range from15 to 70 weight %, more preferably 20 to 65 weight %, more particularly25 to 65 weight %. A composition of this kind exhibits high strength inconjunction with good stretchability.

The composition further comprises at least one amine of the formula (I).

A is preferably selected from the group consisting of 1,2-ethylene,1,2-propylene, 1,3-propylene, 2-methyl-1,5-pentylene, 1,6-hexylene,2,2(4),4-trimethyl-1,6-hexylene, 1,3-cyclohexylenebis(methylene),1,3-phenylenebis(methylene),(1,5,5-trimethylcyclohexan-1-yl)methane-1,3,3-aza-1,5-pentylene,3,6-diaza-1,8-octylene, 3,6,9-triaza-1,11-undecylene,4-aza-1,7-heptylene, 3-aza-1,6-hexylene, 4,7-diaza-1,10-decylene, and7-aza-1,13-tridecylene.

Preferred among these is 1,2-propylene. These amines have a particularlylow tendency toward carbamatization and enable high strengths andparticularly high elongations.

Preference among these is also given to 1,3-phenylenebis(methylene).These amines have a low tendency toward carbamatization and enableparticularly high strengths.

R independently at each occurrence is preferably a hydrogen radical oris methyl, and more particularly is in each case a hydrogen radical.These amines are particularly easy to obtain and have a particularly lowviscosity.

Preferably, Q is an optionally Y-substituted phenyl radical. Theseamines have a particularly low propensity toward carbamatization.

Y preferably represents identical or different radicals selected fromthe group consisting of alkyl, alkoxy and dialkylamino each having 1 to12, especially 1 to 4, carbon atoms. More preferably, Y is methyl or ismethoxy or is dimethylamino. Most preferably, Y is methoxy or isdimethylamino.

Preferably, the Y radical is in the meta and/or para position. Wheren=1, the Y radical is located in particular in the para position.

n is preferably 0 or 1 or 2, more particularly 0 or 1.

More preferably, n is 0. These amines enable particularly goodworkability.

If n is 1, Q is especially a Y-substituted phenyl radical and Y isespecially methoxy or dimethylamino.

More preferably, A is 1,2-propylene, R is a hydrogen radical, Q is aphenyl radical, m is 1, and n is 0. These amines enable especially goodworkability, high strength, and particularly high elongation.

With particular preference, moreover, A is 1,3-phenylenebis(methylene),R is a hydrogen radical, Q is a phenyl radical, m is 1 and n is 0. Thisamine enables particularly good workability and particularly highstrength.

With particular preference, moreover, A is 1,3-phenylenebis(methylene),R in each case is a hydrogen radical, Q is a phenyl radical, m is 2, andn is 0. This amine enables particularly good workability andparticularly high strength. This amine is available commercially as aconstituent of Gaskamine® 240 (from Mitsubishi Gas Chemical).

The amine of the formula (I) is preferably selected from the groupconsisting of N-benzyl-1,2-ethanediamine,N-(4-methoxybenzyl)-1,2-ethanediamine,N-(4-(dimethylamino)benzyl)-1,2-ethanediamine,N¹-benzyl-1,2-propanediamine or N²-benzyl-1,2-propanediamine or amixture of these isomers, N¹-(4-methoxybenzyl)-1,2-propanediamine orN²-(4-methoxybenzyl)-1,2-propanediamine or a mixture of these isomers,N¹-(4-(dimethylamino)benzyl)-1,2-propanediamine orN²-(4-(dimethylamino)benzyl)-1,2-propanediamine or a mixture of theseisomers, N-benzyl-1,3-bis(aminomethyl)benzene andN-phenylethyl-1,3-bis(aminomethyl)benzene.

Preferred among these is N¹-benzyl-1,2-propanediamine orN²-benzyl-1,2-propanediamine or a mixture of these isomers. These aminesare obtainable in particular from the reductive alkylation of1,2-propylenediamine with benzaldehyde and hydrogen. They are used inparticular as a reaction product purified by distillation.

Further preferred among these is N-benzyl-1,3-bis(aminomethyl)benzene.This amine is obtainable in particular from the reductive alkylation of1,3-bis(aminomethyl)benzene with benzaldehyde and hydrogen. It is usedin particular as a reaction product containing fractions ofN,N′-dibenzyl-1,3-bis(aminomethyl)benzene.

Further preferred among these isN-phenylethyl-1,3-bis(aminomethyl)benzene. It is obtainable inparticular from the reaction of 1,3-bis(aminomethyl)benzene withstyrene. It is used in particular as a constituent of the commerciallyavailable Gaskamine® 240 (from Mitsubishi Gas Chemical).

The preferred amines of the formula (I) are notable for particularlyready accessibility, particularly low viscosity, and good propertieswhen used in accordance with the invention.

The composition preferably has a content of amine of the formula (I) inthe range from 1 to 35 weight %, more preferably in the range from 2 to30 weight %.

The amount of amine of the formula (I) in the composition is preferablysuch that the number of amine hydrogens in the amine of the formula (I)corresponds to 25 to 150%, more particularly 30 to 130%, of the numberof epoxide groups present.

In the composition, the weight ratio between the silane-functionalpolymer and the epoxy resin is preferably in the range from 10:90 to90:10, more preferably in the range from 20:80 to 80:20, moreparticularly in the range from 25:75 to 75:25.

The composition preferably further comprises at least one aminosilane orepoxysilane or mercaptosilane.

A suitable epoxysilane is especially 3-glycidoxypropyltrimethoxysilaneor 3-glycidoxypropyldimethoxymethylsilane or3-glycidoxypropyltriethoxysilane.

A suitable mercaptosilane is especially 3-mercaptopropyltrimethoxysilaneor 3-mercaptopropyldimethoxymethylsilane or3-mercaptopropyltriethoxysilane.

With particular preference the composition comprises at least oneaminosilane. A suitable aminosilane is especially selected from thegroup consisting of 3-aminopropyltrimethoxysilane,N-(2-aminoethyl)-3-aminopropyltrimethoxysilane,3-amino-2-methylpropyltrimethoxysilane, 4-aminobutyltrimethoxysilane,4-amino-3,3-dimethylbutyltrimethoxysilane,3-aminopropyldimethoxymethylsilane,N-(2-aminoethyl)-3-aminopropyldimethoxymethylsilane andN-(2-aminoethyl)-N′-[3-(trimethoxysilyl)propyl]ethylenediamine, and alsoanalogs thereof with ethoxy groups instead of the methoxy groups on thesilicon.

Particularly preferred among these is 3-aminopropyltrimethoxysilane,3-aminopropyltriethoxysilane,N-(2-aminoethyl)-3-aminopropyltrimethoxysilane orN-(2-aminoethyl)-3-aminopropyltriethoxysilane.

The composition preferably contains aminosilane in an amount in therange from 0.1% to 10% by weight, especially in the range from 0.2% to7% by weight. Such compositions have high strength.

A high aminosilane content enables a particularly high modulus ofelasticity and particularly high strengths.

The composition is preferably a two-component composition consisting ofa first component and a second component, which are produced, packed andstored separately from one another, the amine of the formula (I) notbeing present in the same component as the epoxy resin.

Any aminosilane or mercaptosilane present is preferably in the samecomponent as the amine of the formula (I).

Any epoxysilane present is preferably in the same component as the epoxyresin.

With preference all the constituents that are reactive toward epoxygroups are not in the same component as the liquid epoxy resin.

In a preferred embodiment of the invention, the composition comprises afirst component comprising

-   -   at least one polymer containing silane groups and    -   at least one liquid epoxy resin,        and a second component comprising    -   at least one amine of the formula (I) and    -   optionally at least one aminosilane.

In a further preferred embodiment of the invention, the compositioncomprises a first component comprising

-   -   at least one polymer containing silane groups,    -   at least one amine of the formula (I), and    -   optionally at least one aminosilane,        and a second component comprising    -   at least one liquid epoxy resin.

With both of these embodiments, the components on their own are eachstable on storage in the absence of moisture. When the two componentsare mixed, primary and/or secondary amino groups react with epoxidegroups that are present. Silane groups react and release alcohol whenthey come into contact with water.

In one embodiment of the invention, the composition comprises water or awater-releasing substance. A composition of this kind is especiallysuitable for applications where the absorption of water from the air orfrom the substrates to which the composition is applied is low.Particular such applications are as an adhesive between materialsimpervious to diffusion, such as metals, plastics, fiber-reinforcedcomposite materials, glass or ceramic, where the adhesive has virtuallyno air contact.

The composition preferably contains a total of up to 1 weight % of freeor releasable water.

In particular, the ratio between the water contained in or released inthe composition and the water required for complete hydrolysis andcrosslinking of the silane groups is at least 0.5, preferably at least1, and at most 5, preferably at most 2.5.

The water may be present in free form or may be bound physically orchemically to a carrier material. Suitable carrier materials for waterare porous materials which enclose water within cavities, especiallykieselguhr or molecular sieves. Other suitable carrier materials arethose which take up water in nonstoichiometric quantities and have apastelike consistency or form gels, examples being silica gels, clays,polysaccharides or polyacrylic acids which are also known as“superabsorbents” and are employed, for example, in the production ofhygiene articles. Carrier materials additionally suitable are polymersin which water can be emulsified such as to form a stable emulsion.

Suitable water-releasing substances are hydrates or aqua complexes,especially inorganic compounds which contain water in coordinativelybonded form or as water of crystallization, more particularlyNa₂SO₄.10H₂O, CaSO₄.2H₂O, CaSO₄½H₂O, Na₂B₄O₇.10H₂O, MgSO₄.7H₂O, thehexaaqua complexes of iron(II), iron(III), cobalt(II), cobalt(III) ornickel(II), [(H₂O)₄Co(NH₃)₂]³⁺ or [Cl(H₂O)₃Co(NH₃)₂]²⁺

Additionally suitable as water-releasing substances are compounds whichrelease water on heating, particularly at a temperature in the rangefrom 50 to 150° C., especially 70 to 130° C., such as, for example,boric acid, aluminum hydroxides or silicas. Especially suitable is boricacid. This compound is preferably in finely dividedly dispersed form.More particularly it has an average particle diameter in the range from0.01 to 100 μm, preferably 0.1 to 50 μm, more particularly 0.3 to 30 μm.

Further suitable water-releasing substances are compounds which are ableto condense with primary amines and release water in the process.

Suitable compounds condensable with primary amines are, in particular:

-   -   ketones, especially acetone, methyl ethyl ketone, methyl        isobutyl ketone, methyl amyl ketone, methyl isoamyl ketone,        cyclohexanone;    -   diketones, especially 1,3-diketones, more particularly        2,4-pentanedione or 3,5-heptanedione, or 1,4-diketones, more        particularly 2,5-hexanedione;    -   aldehydes, especially propanal, 2-methylpropanal, butanal,        2-methylbutanal, 2-ethylbutanal, pentanal, pivalaldehyde,        2-methylpentanal, 3-methylpentanal, 4-methylpentanal,        2,3-dimethylpentanal, hexanal, 2-ethylhexanal, heptanal,        octanal, nonanal, decanal, undecanal, 2-methylundecanal,        dodecanal, methoxyacetaldehyde, cyclopropanecarbaldehyde,        cyclopentanecarbaldehyde, cyclohexanecarbaldehyde,        2,2-dimethyl-3-phenylpropanal, 1-naphthaldehyde, benzaldehyde,        salicylaldehyde, 2-methylbenzaldehyde, 3-methylbenzaldehyde,        4-methylbenzaldehyde, 4-methoxybenzaldehyde,        4-dimethylaminobenzaldehyde,        2,2-dimethyl-3-(N,N-bis(methoxyethyl))aminopropanal,        2,2-dimethyl-3-(N-morpholino)propanal,        2,2-dimethyl-3-(N-(2,6-dimethyl)morpholino)propanal,        2,2-dimethyl-3-acetoxypropanal,        2,2-dimethyl-3-isobutyroxypropanal or        2,2-dimethyl-3-lauroyloxypropanal.

In one embodiment of the invention, the composition comprises at leastone water-releasing substance in the form of a compound condensable withprimary amines. This compound is preferably not in the same component asthe amine of the formula (I).

When the components are mixed, the compound condensable with primaryamines may react with primary amines that are present, the compositionvery quickly producing water in extremely fine division and beingtherefore able to carry out particularly efficient crosslinking of thesilane groups present.

The composition may additionally include in particular at least onefurther amine, which does not conform to the formula (I), and/or atleast one accelerator.

Suitable accelerators are substances which accelerate the crosslinkingof polymers containing silane groups. Particularly suitable for thispurpose are metal catalysts and/or nitrogen-containing compounds.

Suitable metal catalysts are compounds of titanium, zirconium, aluminum,or tin, especially organotin compounds, organotitanates,organozirconates or organoaluminates, these metal catalysts having, inparticular, alkoxy groups, aminoalkoxy groups, sulfonate groups,carboxyl groups, 1,3-diketonate groups, 1,3-ketoesterate groups, dialkylphosphate groups or dialkyl pyrophosphate groups.

Particularly suitable organotin compounds are dialkyltin oxides,dialkyltin dichlorides, dialkyltin dicarboxylates or dialkyltindiketonates, especially dibutyltin oxide, dibutyltin dichloride,dibutyltin diacetate, dibutyltin dilaurate, dibutyltindiacetylacetonate, dioctyltin oxide, dioctyltin dichloride, dioctyltindiacetate, dioctyltin dilaurate or dioctyltin diacetylacetonate, andalso alkyltin thioesters.

Particularly suitable organotitanates arebis(ethylaceto-acetato)diisobutoxytitanium(IV),bis(ethylacetoacetato)diisopropoxytitanium(IV),bis(acetylacetonato)diisopropoxytitanium(IV),bis(acetylacetonato)diisobutoxy-titanium(IV),tris(oxyethyl)amine-isopropoxy-titanium(IV),bis[tris(oxyethyl)-amine]diisopropoxytitanium(IV),bis(2-ethylhexane-1,3-dioxy)titanium(IV),tris[2-((2-aminoethyl)amino)ethoxy]ethoxytitanium(IV),bis(neopentyl(diallyl)oxy)-diethoxytitanium(IV), titanium(IV)tetrabutoxide, tetra(2-ethylhexyloxy) titanate, tetra(isopropoxy)titanate or polybutyl titanate. Especially suitable are the commerciallyavailable products Tyzor® AA, GBA, GBO, AA-75, AA-65, AA-105, DC, BEAT,BTP, TE, TnBT, KTM, TOT, TPT or IBAY (all from Dorf Ketal); Tytan PBT,TET, X85, TAA, ET, S2, S4 or S6 (all from Borica Company Ltd.) andKen-React® KR® TTS, 7, 9QS, 12, 26S, 33DS, 38S, 39DS, 44, 134S, 138S,133DS, 158FS or LICA® 44 (all from Kenrich Petrochemicals).

Particularly suitable organozirconates are the commercially availableproducts Ken-React® NZ® 38J, KZ® TPPJ, KZ® TPP, NZ® 01, 09, 12 38, 44 or97 (all from Kenrich Petrochemicals) or Snapcure® 3020, 3030, 1020 (allfrom Johnson Matthey & Brandenberger).

A particularly suitable organoaluminate is the commercially availableproduct K-Kat 5218 (from King Industries).

Nitrogen-containing compounds with particular suitability asaccelerators are amines such as, in particular, N-ethyldiisopropylamine,N,N,N′,N′-tetramethylalkylenediamines, polyoxyalkyleneamines,1,4-diazabicyclo[2.2.2]octane; amidines such as, in particular,1,8-diazabicyclo[5.4.0]undec-7-ene (DBU),1,5-diazabicyclo[4.3.0]non-5-ene (DBN),6-dibutylamino-1,8-diazabicyclo[5.4.0]undec-7-ene; guanidines such as,in particular, tetramethylguanidine, 2-guanidinobenzimidazole,acetylacetoneguanidine, 1,3-di-o-tolylguanidine,2-tert-butyl-1,1,3,3-tetramethylguanidine, or reaction products ofcarbodiimides and amines such as, in particular, polyetheramines oraminosilanes; or imidazoles such as, in particular,N-(3-trimethoxysilylpropyl)-4,5-dihydroimidazole orN-(3-triethoxysilylpropyl)-4,5-dihydroimidazole.

Also especially suitable are combinations of different accelerators forthe crosslinking of polymers containing silane groups, more particularlycombinations of at least one metal catalyst and at least onenitrogen-containing compound.

Preferred are organotin compounds, organotitanates, amines, amidines,guanidines or imidazoles.

Further substances suitable as accelerators are those which acceleratethe reaction of epoxide groups with amino groups. Suitable for thispurpose are especially acids or compounds hydrolyzable to acids,especially organic carboxylic acids such as acetic acid, benzoic acid,salicylic acid, 2-nitrobenzoic acid, lactic acid, organic sulfonic acidssuch as methanesulfonic acid, p-toluenesulfonic acid or4-dodecylbenzenesulfonic acid, sulfonic esters, other organic orinorganic acids such as, in particular, phosphoric acid, or mixtures ofthe aforementioned acids and acid esters; tertiary amines such as, inparticular, 1,4-diazabicyclo[2.2.2]octane, benzyldimethylamine,α-methylbenzyldimethylamine, triethanolamine, dimethylaminopropylamine,imidazoles such as, in particular, N-methylimidazole, N-vinylimidazoleor 1,2-dimethylimidazole, salts of such tertiary amines, quaternaryammonium salts, such as, in particular, benzyltrimethylammoniumchloride, amidines such as, in particular,1,8-diazabicyclo[5.4.0]undec-7-ene, guanidines such as, in particular,1,1,3,3-tetramethylguanidine, phenols, especially bisphenols, phenolicresins or Mannich bases such as, in particular,2-(dimethylaminomethyl)phenol, 2,4,6-tris(dimethylaminomethyl)phenol orpolymers of phenol, formaldehyde and N,N-dimethylpropane-1,3-diamine,phosphites such as, in particular, di- or triphenyl phosphites, orcompounds having mercapto groups. Preferred are acids, tertiary aminesor Mannich bases. Most preferred is salicylic acid or2,4,6-tris(dimethylaminomethyl)phenol or a combination thereof.

Preferred as further amine are polyamines which have at least threeamine hydrogens reactive toward epoxide groups, more particularly thefollowing polyamines:

-   -   aliphatic, cycloaliphatic or arylaliphatic primary diamines,        especially 2,2-dimethylpropane-1,3-diamine, pentane-1,3-diamine        (DAMP), pentane-1,5-diamine, 1,5-diamino-2-methylpentane (MPMD),        2-butyl-2-ethylpentane-1,5-diamine (C11 neodiamine),        hexane-1,6-diamine, 2,5-dimethylhexane-1,6-diamine,        2,2(4),4-trimethylhexamethylenediamine (TMD),        heptane-1,7-diamine, octane-1,8-diamine, nonane-1,9-diamine,        decane-1,10-diamine, undecane-1,11-diamine,        dodecane-1,12-diamine, 1,2-, 1,3- or 1,4-diaminocyclohexane,        bis(4-aminocyclohexyl)methane (H₁₂-MDA),        bis(4-amino-3-methylcyclohexyl)methane,        bis(4-amino-3-ethylcyclohexyl)methane,        bis(4-amino-3,5-dimethylcyclohexyl)methane,        bis(4-amino-3-ethyl-5-methylcyclohexyl)methane,        1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane        (isophoronediamine or IPDA), 2- or        4-methyl-1,3-diaminocyclohexane or mixtures thereof,        1,3-bis(aminomethyl)cyclohexane,        1,4-bis(aminomethyl)cyclohexane,        2,5(2,6)-bis(aminomethyl)bicyclo[2.2.1]heptane (NBDA),        3(4),8(9)-bis(aminomethyl)tricyclo[5.2.1.0^(2,6)]decane,        1,4-diamino-2,2,6-trimethylcyclohexane (TMCDA),        menthane-1,8-diamine,        3,9-bis(3-aminopropyl)-2,4,8,10-tetraoxaspiro[5.5]undecane,        1,3-bis(aminomethyl)benzene (MXDA) or        1,4-bis(aminomethyl)benzene;    -   aliphatic primary di- or triamines containing ether groups,        especially bis(2-aminoethyl) ether, 3,6-dioxaoctane-1,8-diamine,        4,7-dioxadecane-1,10-diamine, 4,7-dioxadecane-2,9-diamine,        4,9-dioxadodecane-1,12-diamine, 5,8-dioxadodecane-3,10-diamine,        4,7,10-trioxatridecane-1,13-diamine or higher oligomers of these        diamines, bis(3-aminopropyl)polytetrahydrofurans or other        polytetrahydrofurandiamines, diamines containing cycloaliphatic        ether groups from the propoxylation and subsequent amination of        1,4-dimethylolcyclohexane, especially obtainable as Jeffamine®        RFD-270 (from Huntsman), or polyoxyalkylenedi- or -triamines        that are typically products from the amination of        polyoxyalkylenedi- or -triols and are obtainable, for example,        under the Jeffamine® name (from Huntsman), under the        Polyetheramine name (from BASF) or under the PC Amine® name        (from Nitroil). Especially suitable polyoxyalkylenedi- or        -triamines are Jeffamine® D-230, Jeffamine® D-400, Jeffamine®        D-2000, Jeffamine® EDR-104, Jeffamine® EDR-148, Jeffamine®        EDR-176, Jeffamine® T-403, Jeffamine® T-3000, Jeffamine® T-5000,        or corresponding amines from BASF or Nitroil;    -   polyamines having secondary amino groups and having two primary        aliphatic amino groups, such as, in particular,        3-(2-aminoethyl)aminopropylamine, bis(hexamethylene)triamine        (BHMT), diethylenetriamine (DETA), triethylenetetramine (TETA),        tetraethylenepentamine (TEPA), pentaethylenehexamine (PEHA) or        higher homologs of linear polyethyleneamines such as        polyethylenepolyamine having 5 to 7 ethyleneamine units (called        “higher ethylenepolyamine”, HEPA), products from the multiple        cyanoethylation or cyanobutylation and subsequent hydrogenation        of primary di- and polyamines having at least two primary amino        groups, such as dipropylenetriamine (DPTA),        N-(2-aminoethyl)propane-1,3-diamine (N3 amine),        N,N′-bis(3-aminopropyl)ethylenediamine (N4 amine),        N,N′-bis(3-aminopropyl)-1,4-diaminobutane,        N5-(3-aminopropyl)-2-methylpentane-1,5-diamine,        N3-(3-aminopentyl)pentane-1,3-diamine,        N5-(3-amino-1-ethylpropyl)-2-methylpentane-1,5-diamine or        N,N′-bis(3-amino-1-ethylpropyl)-2-methylpentane-1,5-diamine;    -   polyamines having tertiary amino groups, such as, in particular,        N,N-dimethyldi(1,3-propylene)triamine (DMAPAPA),        N,N′-bis(aminopropyl)piperazine,        N,N-bis(3-aminopropyl)methylamine,        N,N-bis(3-aminopropyl)ethylamine,        N,N-bis(3-aminopropyl)propylamine,        N,N-bis(3-aminopropyl)cyclohexylamine,        N,N-bis(3-aminopropyl)-2-ethylhexylamine, products from the        double cyanoethylation and subsequent reduction of fatty amines        derived from natural fatty acids, such as        N,N-bis(3-aminopropyl)dodecylamine or        N,N-bis(3-aminopropyl)tallowalkylamine, available as Triameen®        Y12D or Triameen® YT (from Akzo Nobel);    -   aliphatic, cycloaliphatic or arylaliphatic primary triamines,        especially 4-aminomethyloctane-1,8-diamine,        1,3,5-tris(aminomethyl)benzene,        1,3,5-tris(aminomethyl)cyclohexane, tris(2-aminoethyl)amine,        tris(2-aminopropyl)amine or tris(3-aminopropyl)amine;    -   diamines having one primary and one secondary amino group,        especially products from the reductive alkylation of primary        aliphatic polyamines with aldehydes or ketones, such as, in        particular, N-benzyl-1,3-bis(aminomethyl)benzene,        N-2-ethylhexyl-1,3-bis(aminomethyl)benzene, or partially        styrenized polyamines such as, in particular, styrenized MXDA        (available as Gaskamine® 240 from Mitsubishi Gas Chemical);    -   Mannich bases obtained from the reaction of phenols with        aldehydes, especially formaldehyde, and aliphatic or        cycloaliphatic amines, especially phenalkamines, i.e., Mannich        bases of cardanol (long-chain alk(en)ylphenols and -resorcinols        obtained by thermal treatment of cashewnut-shell oil extracts,        containing as main component        3-(pentadeca-8,11,14-trienyl)phenol, more particularly the        commercial products Cardolite® NC-540, NC-557, NC-558, NC-566,        Lite 2002, GX-6019, GX-6013, NX-4943, NX-5607 or NX-5608 (from        Cardolite), Aradur® 3440, 3441, 3442 or 3460 (from Huntsman), or        Beckopox® EH 614, EH 621, EH 624, EH 628 or EH 629 (from Cytec);    -   aromatic polyamines such as, in particular, m- and        p-phenylenediamine, 4,4′-, 2,4′- and/or        2,2′-diaminodiphenylmethane,        3,3′-dichloro-4,4′-diaminodiphenylmethane (MOCA), tolylene-2,4-        and/or -2,6-diamine, mixtures of 3,5-dimethylthiotolylene-2,4-        and -2,6-diamine (available as Ethacure® 300 from Albermarle),        mixtures of 3,5-diethyltolylene-2,4- and -2,6-diamine (DETDA,        available as Ethacure® 100 from Albermarle),        3,3′,5,5′-tetraethyl-4,4′-diaminodiphenylmethane (M-DEA),        3,3′,5,5′-tetraethyl-2,2′-dichloro-4,4′-diaminodiphenylmethane        (M-CDEA),        3,3′-diisopropyl-5,5′-dimethyl-4,4′-diaminodiphenylmethane        (M-MIPA), 3,3′,5,5′-tetraisopropyl-4,4′-diaminodiphenylmethane        (M-DIPA), 4,4′-diaminodiphenylsulfone (DDS),        4-amino-N-(4-aminophenyl)benzenesulfonamide,        5,5′-methylenedianthranilic acid, dimethyl        5,5′-methylenedianthranilate, propylene        1,3-bis(4-aminobenzoate), butylene 1,4-bis(4-aminobenzoate),        polytetramethylene oxide bis(4-aminobenzoate) (available as        Versalink® from Air Products), 1,2-bis(2-aminophenylthio)ethane,        2-methylpropyl 4-chloro-3,5-diaminobenzoate or tert-butyl        (4-chloro-3,5-diaminobenzoate);    -   polyamidoamines, especially reaction products of a mono- or        polybasic carboxylic acid, or the esters or anhydrides thereof,        especially a dimer fatty acid, with an aliphatic, cycloaliphatic        or aromatic polyamine used in a stoichiometric excess,        especially a polyalkyleneamine, for example DETA or TETA,        especially the commercially available polyamidoamines Versamid®        100, 125, 140 or 150 (from Cognis), Aradur® 223, 250 or 848        (from Huntsman), Euretek® 3607 or 530 (from Huntsman) or        Beckopox® EH 651, EH 654, EH 655, EH 661 or EH 663 (from Cytec);    -   or adducts of polyamines with epoxides or epoxy resins,        especially adducts with diepoxides in a molar ratio of about        2/1, or adducts with monoepoxides in a molar ratio of about 1/1,        or reaction products of polyamines and epichlorohydrin,        especially that of 1,3-bis(aminomethyl)benzene, commercially        available as Gaskamine® 328 (from Mitsubishi Gas Chemical).

Preferred as further amine are primary aliphatic diamines having amolecular weight of at least 120 g/mol, especially at least 150 g/mol,preferably TMD, H₁₂-MDA, IPDA, 2- or 4-methyl-1,3-diaminocyclohexane ormixtures thereof, 1,3-bis(aminomethyl)cyclohexane,1,4-bis(aminomethyl)cyclohexane, NBDA, MXDA or BHMT, especially TMD,H₁₂-MDA, IPDA, NBDA, or BHMT.

Preferred as further amine are also aliphatic primary di- or triaminescontaining ether groups, especially polyoxyalkylenedi- or -triamineshaving an average molecular weight in the range from 200 to 500 g/mol,especially Jeffamine® D-230 or Jeffamine® D-400 or Jeffamine® T-403 (allfrom Huntsman), or cycloaliphatic diamines containing ether groups fromthe propoxylation and subsequent amination of 1,4-dimethylolcyclohexane,especially Jeffamine® RFD-270 (from Huntsman).

Preferred as further amine are also adducts, containing at least threeamine hydrogens, of at least one polyamine having 2 to 12 carbon atomsand at least one epoxide, more particularly an adduct which contains atleast three amine hydrogens and is the adduct of at least one polyaminewith at least one aromatic monoepoxide, the molar ratio of this reactionhaving been around 1/1. The polyamine was especially present in excessduring the reaction and has been removed by means of distillation afterthe reaction. A preferred aromatic monoepoxide is cresyl glycidyl etherand a preferred polyamine is 1,2-ethylenediamine, 1,2-propylenediamine,1,3-propylenediamine or MPMD, especially 1,2-propylenediamine or MPMD.

Further amines are present in the composition preferably in an amountsuch that at most 60%, especially at most 45%, of the amine hydrogens inthe composition originate from further amines.

The composition is preferably largely free of amines having a molecularweight below 150 g/mol, especially below 120 g/mol. It preferablycontains less than 1 weight %, especially less than 0.5 weight %, ofamines having a molecular weight below 150 g/mol, especially below 120g/mol. A composition of this kind is particularly advantageous in termsof toxicology and odor.

The composition may comprise further substances reactive toward epoxidegroups, examples being monoamines such as hexylamine or benzylamine orpolyethermonoamines, especially alcohol-started products such asJeffamine® M-600, Jeffamine® M-1000, Jeffamine® M-2005, Jeffamine®M-2070, Jeffamine® XTJ-581, Jeffamine® XTJ-249 or Jeffamine® XTJ-435, oralkylphenol-started products such as Jeffamine® XTJ-436 (all fromHuntsman), or compounds containing mercapto groups, especially thefollowing:

-   -   liquid mercaptan-terminated polysulfide polymers, known by the        Thiokol® brand name (from Morton Thiokol; available, for        example, from SPI Supplies, or from Toray Fine Chemicals),        especially the LP-3, LP-33, LP-980, LP-23, LP-55, LP-56, LP-12,        LP-31, LP-32 or LP-2 products; and also known by the Thioplast®        brand name (from Akzo Nobel), especially the G 10, G 112, G 131,        G 1, G 12, G 21, G 22, G 44 or G 4 products;    -   mercaptan-terminated polyoxyalkylene ethers obtainable, for        example, by reaction of polyoxyalkylenedi- or -triols either        with epichlorohydrin or with an alkylene oxide, followed by        sodium hydrogensulfide;    -   mercaptan-terminated compounds in the form of polyoxyalkylene        derivatives, known by the Capcure® brand name (from Cognis),        especially the WR-8, LOF or 3-800 products;    -   polyesters of thiocarboxylic acids, for example pentaerythritol        tetramercaptoacetate, trimethylolpropane trimercaptoacetate,        glycol dimercaptoacetate, pentaerythritol        tetra(3-mercaptopropionate), trimethylolpropane        tri(3-mercaptopropionate) or glycol di(3-mercaptopropionate), or        esterification products of polyoxyalkylenediols or -triols,        ethoxylated trimethylolpropane or polyester diols with        thiocarboxylic acids such as thioglycolic acid or 2- or        3-mercaptopropionic acid; or    -   further compounds having mercapto groups, such as, in        particular, 2,4,6-trimercapto-1,3,5-triazine,        2,2′-(ethylenedioxy)diethanethiol (triethylene glycol        dimercaptan) or ethanedithiol.

Further suitable constituents of the composition are in particular thefollowing auxiliaries and adjuvants:

-   -   adhesion promoters and/or crosslinkers, especially        (meth)acrylosilanes, anhydridosilanes, carbamatosilanes,        alkylsilanes or iminosilanes, or oligomeric forms of these        silanes, or adducts of primary aminosilanes with epoxysilanes or        (meth)acrylosilanes or anhydridosilanes;    -   plasticizers, especially carboxylic esters such as phthalates,        especially diisononyl phthalate (DINP), diisodecyl phthalate        (DIDP) or di(2-propylheptyl) phthalate (DPHP), hydrogenated        phthalates, especially hydrogenated diisononyl phthalate        (DINCH), terephthalates, especially dioctyl terephthalate,        trimellitates, adipates, especially dioctyl adipate, azelates,        sebacates, polyols, especially polyoxyalkylene polyols or        polyester polyols, benzoates, glycol ethers, glycol esters,        organic phosphoric, phosphonic or sulfonic esters, polybutenes,        polyisobutenes, or plasticizers derived from natural fats or        oils, especially epoxidized soybean oil or linseed oil;    -   solvents, diluents or extenders, such as especially xylene,        2-methoxyethanol, dimethoxyethanol, 2-ethoxyethanol,        2-propoxyethanol, 2-isopropoxyethanol, 2-butoxyethanol,        2-phenoxyethanol, 2-benzyloxyethanol, benzyl alcohol, ethylene        glycol, ethylene glycol dimethyl ether, ethylene glycol diethyl        ether, ethylene glycol dibutyl ether, ethylene glycol diphenyl        ether, diethylene glycol, diethylene glycol monomethyl ether,        diethylene glycol monoethyl ether, diethylene glycol        mono-n-butyl ether, diethylene glycol dimethyl ether, diethylene        glycol diethyl ether, diethylene glycol di-n-butyl ether,        propylene glycol butyl ether, propylene glycol phenyl ether,        dipropylene glycol, dipropylene glycol monomethyl ether,        dipropylene glycol dimethyl ether, dipropylene glycol di-n-butyl        ether, N-methylpyrrolidone, diphenylmethane,        diisopropylnaphthalene, mineral oil fractions, for example        Solvesso® products (from Exxon), alkylphenols such as        tert-butylphenol, nonylphenol, dodecylphenol or cardanol (from        cashewnut-shell oil, containing, as main constituent,        3-(8,11,14-pentadecatrienyl)phenol), styrenized phenol,        bisphenols, aromatic hydrocarbon resins, especially types        containing phenol groups, alkoxylated phenol, especially        ethoxylated or propoxylated phenol, especially 2-phenoxyethanol,        adipates, sebacates, phthalates, benzoates, organic phosphoric        or sulfonic esters or sulfonamides;    -   reactive diluents, especially reactive diluents for epoxy resins        such as cresyl glycidyl ether, benzyl glycidyl ether,        tert-butylphenyl glycidyl ether, nonylphenyl glycidyl ether,        2-ethylhexyl glycidyl ether, glycidyl ethers of natural alcohols        such as, in particular, C₈- to C₁₀-alkyl glycidyl ethers or C₁₂-        to C₁₄-alkyl glycidyl ethers, or glycidyl ethers of diols or        polyols such as polypropylene glycols, dimethylolcyclohexane,        glycerol, neopentyl glycol or trimethylolpropane, or,        additionally, epoxidized natural oils such as soybean oil,        linseed oil or palm kernel oil, or compounds containing        acetoacetate groups, especially acetoacetylated polyols, or        butyrolactone or carbonates or aldehydes or isocyanates, or        silicones containing reactive groups;    -   inorganic or organic fillers, especially ground or precipitated        calcium carbonates, optionally coated with fatty acids,        especially stearates; baryte (heavy spar), talc, quartz flour,        quartz sand, iron mica, dolomite, wollastonite, kaolin, mica        (potassium aluminum silicate), molecular sieve, aluminum oxide,        aluminum hydroxide, magnesium hydroxide, silica, cement, gypsum,        fly ash, carbon black, graphite, metal powders such as aluminum,        copper, iron, zinc, silver or steel, PVC powders or hollow        spheres;    -   fibers, especially glass fibers, carbon fibers, metal fibers,        ceramic fibers, polymer fibers such as polyamide fibers or        polyethylene fibers, or natural fibers such as wool, cellulose,        hemp or sisal;    -   inorganic or organic pigments, especially titanium dioxide,        chromium oxide or iron oxide;    -   dyes;    -   dryers, especially tetraethoxysilane, vinyltrimethoxysilane,        vinyltriethoxysilane or organosilanes having a functional group        in the a position to the silane group, especially        N-(methyldimethoxysilylmethyl)-O-methylcarbamate,        (methacryloyloxymethyl)silanes, methoxymethylsilanes,        orthoformic esters, and also calcium oxide or molecular sieves;    -   rheology modifiers, especially thickeners, especially sheet        silicates such as bentonites, derivatives of castor oil such as        hydrogenated castor oil, polyamides, polyurethanes, urea        compounds, polyvinyl chlorides, fumed silicas;    -   natural resins, fats or oils such as rosin, shellac, linseed        oil, castor oil or soybean oil;    -   nonreactive polymers, especially homo- or copolymers of        unsaturated monomers, especially from the group comprising        ethylene, propylene, butylene, isobutylene, isoprene, vinyl        acetate or alkyl (meth)acrylates, especially polyethylenes (PE),        polypropylenes (PP), polyisobutylenes, ethylene-vinyl acetate        copolymers (EVA) or atactic poly-α-olefins (APAO);    -   flame-retardant substances, especially the aluminum hydroxide or        magnesium hydroxide fillers already mentioned, or boron        compounds, antimony trioxide or phosphorus, or, in particular,        organic phosphoric esters such as, in particular, triethyl        phosphate, tricresyl phosphate, triphenyl phosphate, diphenyl        cresyl phosphate, isodecyl diphenyl phosphate,        tris(1,3-dichloro-2-propyl) phosphate, tris(2-chloroethyl)        phosphate, tris(2-ethylhexyl) phosphate, tris(chloroisopropyl)        phosphate, tris(chloropropyl) phosphate, isopropylated triphenyl        phosphate, mono-, bis- or tris(isopropylphenyl) phosphates of        different degrees of isopropylation, resorcinol bis(diphenyl        phosphate), bisphenol A bis(diphenyl phosphate) or ammonium        polyphosphates; or    -   additives, especially wetting agents, flow control agents,        defoamers, deaerators, stabilizers against oxidation, heat,        light or UV radiation, or biocides.

It may be useful to dry certain constituents chemically or physicallybefore mixing them into the composition, particularly if they are to bestored together with the polymer containing silane groups.

In the case of a two-component composition, such further constituentsmay be part of the first component or of the second component. Freewater is preferably not in the same component as the polymer containingsilane groups. Further constituents that are reactive toward epoxidegroups are preferably not in the same component as the epoxy resin.

In the composition, the ratio between the number of groups reactivetoward epoxide groups relative to the number of epoxide groups ispreferably in the range from 0.5 to 1.5, especially in the range from0.8 to 1.2.

The composition preferably contains only a low content of solvents. Itcontains preferably 200 g VOC per liter or less, especially 150 g VOCper liter or less, more preferably 100 g VOC per liter or less, verypreferably 50 g VOC per liter or less. In particular it is largely freeof solvents.

The composition is in particular produced and used as a two-componentcomposition. In this case the two components are produced and storedseparately in the absence of moisture. They are typically each stored ina separate container. The separate components are storage-stable; thismeans that each component can be stored prior to use for several monthsup to half a year or longer, without any change in their respectiveproperties to an extent relevant to their service. A suitable containerfor storage of the respective component is especially a vat, a hobbock,a pouch, a bucket, a can, a cartridge or a tube.

For the use of the composition, the two components are mixed with oneanother shortly before or during the application. The mixing ratio isselected preferably such that the groups reactive toward epoxide groupsare present in a suitable ratio to the epoxide groups, as describedabove. In parts by weight, the mixing ratio between the two componentsis typically in the range from 1:10 to 10:1.

The two components are mixed by a suitable method; mixing may take placecontinuously or batchwise, using a static mixer or by means of a dynamicmixer. If the mixing precedes the application, care must be taken toensure that application takes place within the open time or potlife ofthe composition, since otherwise there may be disruptions, such asretarded or incomplete development of adhesion to the substrate orpremature gelling, for example. The “open time” or else “potlife” hereis the time which elapses between the mixing of the components and thepoint in time at which it is no longer possible for composition to beproperly applied. A typical measure of the end of the potlife is theattainment of a defined viscosity value.

Mixing takes place preferably at ambient temperature, which is typicallywithin the range from about 5 to 50° C., preferably at about 10 to 30°C.

Curing by chemical reaction begins with the mixing of the twocomponents. Here, the epoxide groups enter into a ring-opening reactionwith primary and secondary amino groups to form amino alcohol units.Further epoxide groups react with themselves in anionic polymerization.The silane groups undergo hydrolysis with release of alcohol, formingsilanol groups (Si—OH groups) and, through subsequent condensationreactions, siloxane groups (Si—O—Si groups). As a result of these andpossibly further reactions, the composition cures to give a crosslinkedpolymer. If the water for hydrolysis of the silane groups was notalready present in the composition or has been released therein, it maycome from the air (atmospheric humidity) or from a substrate, or thecomposition may be contacted, by coating, spraying or mixedincorporation, for example, with a water-containing component.

Curing takes place in particular at a temperature in the range from 0 to150° C. It may in particular take place at ambient temperature, in whichcase it extends typically over several days to weeks until it is largelyat an end under the prevailing conditions. Alternatively, curing maytake place at elevated temperature, more particularly at a temperaturein the range from 50 to 130° C. In certain cases it may be advantageousfor a composition partly cured at ambient temperature to be aftercuredor completely cured at an elevated temperature.

The curing profile of the composition is preferably such as on the onehand to ensure a sufficient potlife or open time, for correctapplication of the composition, and such that on the other hand thecuring has rapidly advanced to a point where the composition can bereleased for traffic or can be worked on further, or where a bondimplemented using the composition is self-supporting and can betransported.

A further subject of the invention is therefore a cured compositionobtained from the composition described by mixing all of the ingredientsand/or components of the composition, applying the mixed composition,and curing the applied composition.

The cured composition has outstanding mechanical properties, very goodthermal stability and good adhesion properties. Depending on the natureand amount of the ingredients, the mechanical properties can be adjustedfrom very elastic, with not too high a modulus of elasticity and withhigh strength, through to tough elastic, with a very high modulus ofelasticity and very high strength. As a result, the composition issuitable for a multiplicity of applications.

The composition is especially suitable for use as adhesive, sealant,coating, casting compound or matrix resin for construction andindustrial applications. As adhesive, the composition is especiallysuitable for structural bonding in the construction or manufacturingindustries, more particularly as assembly adhesive, anchoring adhesive,bodywork adhesive, element adhesive for bridges, for example, sandwichelement adhesive, architectural facing element adhesive, reinforcingadhesive or half-shell adhesive for rotor blades. As a sealant, thecomposition is especially suitable for the sealing of joints, gaps,seams or vacancies of all kinds, particularly in the construction andmanufacturing industries.

As a coating, the composition is especially suitable as a covering,coating, paint, varnish, seal, priming coat or primer for constructionand industrial applications, more particularly as a floor coating forinteriors or in the exterior segment for balconies, patios, parkinglevels, bridges or roofs, or as a protective coating for concrete,cement, metals, plastics or wood. After such a coating has been appliedand—at least partly—cured, a further coating, a further covering or afurther paint coat may be applied to it, this further coat being able tobe likewise a composition of the invention or a different material, moreparticularly an epoxy resin coating or a polyurethane or polyureacoating. As a casting compound, the composition is especially suitableas an electrical encapsulating compound.

As a matrix resin, the composition is especially suitable as a fibercomposite matrix for fiber composite materials such as CRP or GRP.

The composition is especially suitable for use as an adhesive and/orsealant or as a coating.

The composition here is particularly suitable for the bonding, sealingor coating of the following substrates:

-   -   glass, glass-ceramic, screen-printed ceramic, concrete, mortar,        brick, tile, gypsum, natural rocks such as granite or marble, or        glass mineral fiber mats;    -   metals or alloys such as aluminum, iron, steel and nonferrous        metals, or surface-finished metals or alloys such as galvanized        or chromed metals;    -   leather, textiles, paper, wood, woodbase materials bonded with        resins, e.g. phenolic, melamine or epoxy resins, resin-textile        composites or further polymer composites;    -   polymers, especially rigid or flexible PVC, ABS, polycarbonate        (PC), polyamide (PA), polyesters, PMMA, epoxy resins, PUR, POM,        PO, PE, PP, EPM or EPDM, where the polymers have optionally been        surface-treated by means of plasma, corona or flames;    -   fiber-reinforced plastics, such as carbon fiber-reinforced        plastics (CRP), glass fiber-reinforced plastics (GRP) or sheet        molding compounds (SMC);    -   coated substrates such as powder-coated metals or alloys;    -   paints or varnishes, especially automotive topcoats.

The substrates can be pretreated if required prior to the application ofthe composition. Pretreatments of this kind especially include physicaland/or chemical cleaning methods, for example sanding, sandblasting,shotblasting, brushing and/or blowing, and also treatment withdetergents or solvents, or the application of an adhesion promoter, anadhesion promoter solution or a primer.

The result of use as adhesive and/or sealant or coating is an articlebonded and/or sealed or coated with the composition. The article, then,comprises an at least partly cured composition as described above.

The article is more particularly a house, a bathroom, a kitchen, a roof,a balcony, a patio, a parking level, a bridge, a tunnel, a road, asandwich element of a lightweight structure, a solar panel such asphotovoltaic or solarthermal modules, a glass architectural facingelement, a window, a sheet, a mirror, a basin, a white good, a householdappliance, a dishwasher, a washing machine, an oven, a wind turbinerotor blade, an automobile, a bus, a truck, a rail vehicle, a boat, anaircraft, a helicopter, or a headlight; or a component for installationin or on such an article.

EXAMPLES

Adduced hereinafter are working examples which are intended to elucidatethe invention described in detail. It will be appreciated that theinvention is not restricted to these described working examples.

“ANEW” stands for amine hydrogen equivalent weight.

“EEW” stands for epoxy equivalent weight.

“Standard conditions” refer to a temperature of 23±1° C. and a relativeair humidity of 50±5%. “SC” stands for “standard conditions”.

Description of Measuring Methods:

Viscosity was measured on a thermostated Rheotec RC30 cone-plateviscometer (cone diameter 50 mm, cone angle 1°, cone tip-plate distance0.05 mm, shear rate 10 rpm).

Amine value was determined by means of titration (with 0.1N HClO₄ inacetic acid versus crystal violet).

Polymer Containing Silane Groups Used:

STP Polymer-1: In the absence of moisture, 1000 g of Acclaim® 12200polyol (from Bayer; low monol polyoxypropylenediol, OH number 11.0 mgKOH/g, water content around 0.02 wt %), 43.6 g of isophoronediisocyanate (Vestanat® IPDI from Evonik Industries), 126.4 g ofdiisodecyl phthalate and 0.12 g of dibutyltin dilaurate were heated to90° C. with continuous stirring and left at this temperature until thefree isocyanate group content as determined by titrimetry had reached avalue of 0.63 wt %. Subsequently, 62.3 g of diethylN-(3-trimethoxysilylpropyl)aminosuccinate were mixed in and the mixturewas stirred at 90° C. until it was no longer possible to detect any freeisocyanate by means of FT-IR spectroscopy. The silane-functional polymerwas cooled to room temperature and stored in the absence of moisture. Itwas liquid at room temperature and had a viscosity at 20° C. of 99 Pa·s.

STP Polymer-1 contains 10 weight % of plasticizer (diisodecylphthalate).

Epoxy Resin Used: Araldite® GY 250:

bisphenol A diglycidyl ether, EEW 187.5 g/eq (from Huntsman)

Amines of the Formula (I) Used:

N-Benzylpropane-1,2-diamine:

A round-bottom flask was initially charged with 444.8 g (6 mol) ofpropane-1,2-diamine under a nitrogen atmosphere at room temperature.With good stirring, a solution of 212.2 g (2 mol) of benzaldehyde in1500 mL of isopropanol was slowly added dropwise, and the mixture wasstirred for 2 hours. The reaction mixture was then hydrogenated in acontinuous hydrogenation apparatus with a Pd/C fixed bed catalyst at ahydrogen pressure of 90 bar, a temperature of 85° C. and a flow rate of5 mL/min. To monitor the reaction, IR spectroscopy was used to checkwhether the imine band at about 1665 cm⁻¹ had disappeared. Thereafter,the hydrogenated solution was concentrated on a rotary evaporator at 65°C., removing unreacted propane-1,2-diamine and isopropanol. A clear,pale yellowish liquid was obtained. 300 g of this were distilled at 80°C. under reduced pressure, with collection of 237.5 g of distillate at avapor temperature of 60 to 63° C. and 0.08 to 0.09 bar. A colorlessliquid having an amine value of 682 mg KOH/g was obtained, which, by ¹HNMR, was a mixture of N¹-benzylpropane-1,2-diamine andN²-benzylpropane-1,2-diamine in a ratio of about 2/1 and had a GC purityof >97%.

Gaskamine® 240:

styrenized 1,3-bis(aminomethyl)benzene, AHEW 103 g/eq (from MitsubishiGas Chemical)

Further Substances Used:

-   DBTDL 10%: dibutyltin(IV) dilaurate, 10% by weight in diisodecyl    phthalate-   Silquest® A-1120: N-(2-aminoethyl)-3-aminopropyltrimethoxysilane,    AHEW 74.1 g/eq (from Momentive)-   Ancamine® K54: 2,4,6-tris(dimethylaminomethyl)phenol (from Air    Products)-   Jeffamine® D-230: polyetherdiamine with average molecular weight of    230 g/mol, AHEW 60 g/eq (from Huntsman)-   Jeffamine® D-400: polyetherdiamine with average molecular weight of    430 g/mol, AHEW 115 g/eq (from Huntsman)-   Vestamin® TMD: 2,2(4),4-trimethylhexamethylenediamine, AHEW 39.6    g/eq (from Evonik)-   Vestamin® IPD: 3-aminomethyl-3,5,5-trimethylcyclohexylamine, AHEW    42.6 g/eq (from Evonik)-   EP adduct 1: reaction product of 1,5-diamino-2-methylpentane and    Araldite® DY-K, prepared as described hereinafter; AHEW 106.5 g/eq

EP adduct 1 was prepared by heating an initial charge of 4.65 kg of1,5-diamino-2-methylpentane (Dytek® A from Invista) under a nitrogenatmosphere to 70° C. and then, with good stirring, slowly adding 1.83 kgof Araldite® DY-K, in the course of which the temperature of thereaction mixture was 70 to 80° C. After 1 hour at 80° C., the reactionmixture was cooled down and 1,5-diamino-2-methylpentane and furthervolatile constituents were removed by distillation by means of athin-film evaporator (0.5-1 mbar, jacket temperature 160° C.).

Production of Two-Component Compositions:

For each example, the ingredients specified in tables 1 to 3 were mixedin the specified amounts (in parts by weight) of component-1 by means ofa centrifugal mixer (SpeedMixer™ DAC 150, FlackTek Inc.) and stored withexclusion of moisture.

Similarly, the ingredients of component-2 specified in tables 1 to 3were processed and stored.

Subsequently, the two components of each composition were processed bymeans of the centrifugal mixer to give a homogeneous liquid and this wastested immediately as follows:

1 minute after mixing, the viscosity was determined at 20° C.

To measure the time until the composition became free from tack,abbreviated to “TFT”, a small portion of the mixed composition at roomtemperature was applied in a layer thickness of around 3 mm to cardboardand, under standard conditions, a determination was made of the timewhich elapsed until an LDPE pipette used to gently touch the surface ofthe composition for the first time no longer had any residues left onit.

The tensile strength, the elongation at break and the elasticity modulusat 0.5 to 5.0% elongation (modulus of elasticity 5%) were determinedaccording to DIN EN 53504 on flat specimens with a length of 75 mm, witha gage length of 30 mm and a gage width of 4 mm, produced by punchingfrom films with a thickness of around 2 mm of the composition curedunder the respective reported conditions. The values designated by “10dSC” and “14d SC” in the tables were determined after storage times of 10and 14 days, respectively, under standard conditions. The valuesdesignated “+2d 80° C.” were determined on flat specimens which had beenstored for 10 days under standard conditions and subsequently for 2 daysin a forced air oven at 80° C. For examples Z-1 to Z-7 and Ref-1 toRef-4, these values were determined with a pulling speed of 200 mm/min.For examples Z-8 to Z-10 and Ref-5 to Ref-8, they were determined with apulling speed of 10 mm/min.

Shore A hardness was determined according to DIN 53505 on test specimenscured under standard conditions for 14 days. The value in this case wasdetermined in each case on the top, on the side of the test specimenfacing the air. Additionally, the test specimen was turned over and adetermination was likewise made on the bottom, on the side not exposedto the air. The two values are reported as “top/bottom” in table 2.Here, values for top and bottom that are very similar are a sign ofcomplete and undisrupted curing.

After 14 days under SC, the appearance of all the films was ratedvisually. After curing, all of the films were absolutely nontacky, freefrom blisters, and either nontransparently white, or opaque tosemitransparent (referred to as “opaque-transparent”), or almosttransparent, or transparent, in each case with a glossy to silk-mattsurface. Example Ref-4 showed streaking on the surface. The results arereported in tables 1 to 3.

Examples Z-1 to Z-10 are inventive compositions. Examples Ref-1 to Ref-8are comparative examples.

TABLE 1 Composition and properties of examples Z-1 to Z-3 and ofcomparative examples Ref-1 to Ref-2. Example Z-1 Z-2 Z-3 Ref-1 Ref-2Component-1: STP Polymer-1 53.0 53.0 53.0 53.0 53.0 Araldite ® GY 25038.0 38.0 38.0 38.0 38.0 DBTDL 10% 2.0 2.0 2.0 2.0 2.0 Dioctyl adipate7.0 7.0 7.0 7.0 7.0 Component-2: Silquest ® A-1120 2.5 2.5 2.5 2.5 2.5N-Benzylpropane- 10.4 7.0 — — — 1,2-diamine Gaskamine ® 240 — — 19.5 — —Jeffamine ® D-230 — — — 11.4 — Jeffamine ® D-400 — 7.0 — — 21.8Ancamine ® K54 1.2 1.2 1.2 1.2 1.2 Viscosity [Pa · s] 11.7 10.8 13.812.1 7.1 TFT [min.] 35 30 35 40 35 Appearance almost opaque- trans-almost trans- trans- trans- parent trans- parent parent parent parent 10d SC: Tensile strength 8.7 9.8 7.4 6.9 6.0 [MPa] Elongation at break140% 139% 93% 103% 71% Modulus of elasticity 48.4 26.0 66.5 39.1 40.8 5%[MPa] Tear resist. [N/mm] 20.2 14.1 21.2 13.5 14.3 “Tear resist.” standsfor “tear resistance”

TABLE 2 Composition and properties of examples Z-4 to Z-7 and ofcomparative examples Ref-3 to Ref-4. Example Z-4 Z-5 Ref-3 Z-6 Z-7 Ref-4Component-1: STP Polymer-1 50.0 50.0 50.0 40.0 40.0 40.0 Araldite ® GY250 48.0 48.0 48.0 48.0 48.0 48.0 DBTDL 10% 2.0 2.0 2.0 2.0 2.0 2.0Dioctyl adipate — — — 5.0 5.0 5.0 Vinyltrimethoxysilane — — — 5.0 5.05.0 Component-2: Silquest ® A-1120 0.3 0.6 0.6 0.3 0.6 0.6N-Benzylpropane-1,2-diamine 15.3 — — 15.3 — — Gaskamine ® 240 — 28.7 — —28.7 — Jeffamine ® D-400 — — 23.9 — — 23.9 Vestamin ® TMD — — 2.8 — —2.8 Ancamine ® K54 0.4 0.8 0.7 0.4 0.8 0.7 Viscosity [Pa · s] 34.4 37.724.4 7.9 9.5 6.4 TFT [min.] 40 110 40 85 100 40 Appearance opaque-opaque- opaque- opaque- opaque- opaque- transp. transp. transp. transp.transp. transp., streaking 14 d SC: Tensile strength [MPa] 4.9 7.4 6.74.2 6.6 6.1 Elongation at break 120% 81% 80% 80% 67% 61% Modulus ofelasticity 5% [MPa] 5.6 7.9 13.2 8.3 11.7 10.3 Tear resist. [N/mm] 5.05.2 6.5 6.2 6.0 8.3 Shore A top/bottom 78/75 80/79 88/78 75/74 82/8081/74 “Tear resist.” stands for “tear resistance”; “transp.” stands for“transparent”

TABLE 3 Composition and properties of examples Z-8 to Z-10 and ofcomparative examples Ref-5 to Ref-8. Example Z-8 Z-9 Z-10 Ref-5 Ref-6Ref-7 Ref-8 Component-1: STP Polymer-1 32.8 32.8 32.8 32.8 32.8 32.832.8 Araldite ® GY 250 66.5 66.5 66.5 66.5 66.5 66.5 66.5 DBTDL 10% 0.70.7 0.7 0.7 0.7 0.7 0.7 Component-2: Silquest ® A-1120 5.0 5.0 5.0 5.05.0 5.0 5.0 N-Benzylpropane- 17.0 8.5 — — — — — 1,2-diamine Gaskamine ®240 — — 33.0 — — — — Jeffamine ® D-230 — 9.5 — 19.0 — — — Vestamin ® TMD— — — — 13.0 — — Vestamin ® IPD — — — — — 14.0 — EP adduct 1 — — — — — —34.0 Viscosity [Pa · s] 6.6 6.3 8.7 5.6 7.4 11.3 21.4 TFT [min.] 140 120105 120 91 100 90 Appearance nontransp. opaque- opaque- opaque-nontransp. nontransp. nontransp. white transp. transp. transp. whitewhite white 10 d SC Tensile strength 10.3 11.7 14.0 11.3 3.6 4.8 4.9[MPa] Elongation at  8% 10% 12%  9%  8%  9% 66% break Modulus of 188 186149 183 47 58 21 elasticity 5% [MPa] +2 d 80° Tensile strength 11.6 15.218.2 14.2 3.6 4.9 4.0 [MPa] Elongation at  6%  8% 10% 14%  6%  5% 16%break Modulus of 206 243 231 209 59 86 46 elasticity 5% [MPa]“nontransp.” stands for “nontransparent” “transp.” stands for“transparent”

1. A composition comprising at least one polymer containing silanegroups, at least one epoxy resin, and at least one amine of the formula(I)

where A is an alkylene radical having 2 to 15 carbon atoms whichcontains one or more nitrogen atoms, R each independently is a hydrogenor methyl or phenyl radical, Q is a five-, six- or seven-memberedcycloalkyl or aryl radical having an oxygen, sulfur or nitrogen atom inthe ring and having 4 to 7 carbon atoms, Y represents identical ordifferent radicals selected from the group consisting of alkyl, alkoxyand dialkylamino having 1 to 18 carbon atoms, m is 1 or 2, and n is 0 or1 or 2 or
 3. 2. The composition as claimed in claim 1, wherein thepolymer containing silane groups is a polyether containing silanegroups.
 3. The composition as claimed in claim 1, wherein it has acontent of polymer containing silane groups in the range from 5 to 80weight %.
 4. The composition as claimed in claim 1, wherein the epoxyresin is a liquid resin based on a diglycidyl ether of bisphenol A, ofbisphenol F or of bisphenol A/F.
 5. The composition as claimed in claim1, wherein it has an epoxy resin content in the range from 15 to 70weight %.
 6. The composition as claimed in claim 1, wherein A is1,2-propylene, R is a hydrogen radical, Q is a phenyl radical, m is 1and n is
 0. 7. The composition as claimed in claim 1, wherein A is1,3-phenylenebis(methylene), R is a hydrogen radical, Q is a phenylradical, m is 1 and n is
 0. 8. The composition as claimed in claim 1,wherein A is 1,3-phenylenebis(methylene), R in each case is a hydrogenradical, Q is a phenyl radical, m is 2 and n is
 0. 9. The composition asclaimed in claim 1, wherein it has a content of amine of the formula (I)in the range from 1 to 35 weight %.
 10. The composition as claimed inclaim 1, wherein it additionally comprises at least one aminosilane. 11.The composition as claimed in claim 1, wherein it is a two-componentcomposition consisting of a first component and a second component,which are produced, packed and stored separately from one another, theamine of the formula (I) not being present in the same component as theepoxy resin.
 12. The composition as claimed in claim 1, wherein itadditionally comprises at least one further amine, which does notconform to the formula (I), and/or at least one accelerator.
 13. A curedcomposition obtained from the composition as claimed in claim 1 bymixing all of the ingredients and/or components of the composition,applying the mixed composition and curing the applied composition.
 14. Amethod comprising applying the composition as claimed in claim 1 asadhesive and/or sealant or as coating.
 15. A bonded and/or sealed orcoated article obtained from the method as claimed in claim 14.